NDLI: Towards the total synthesis of chondrochloren A: synthesis of the (Z)-enamide fragment

Content Provider	Semantic Scholar
Author	Geldsetzer, Jan Kalesse, Markus
Copyright Year	2020
Abstract	The stereoselective synthesis of the (Z)-enamide fragment of chondrochloren (1) is described. A Buchwald-type coupling between amide 3 and (Z)-bromide 4 was used to generate the required fragment. The employed amide 3 comprising three chiral centers was obtained through a seven-step sequence starting from ᴅ-ribonic acid-1,4-lactone. The (Z)-vinyl bromide 4 is accessible in four steps from 4-hydroxybenzaldehyde. The pivotal cross coupling between both fragments was achieved after extensive experimentation with copper(I) iodide, K2CO3 and N,N′-dimethylethane-1,2-diamine.
Starting Page	670
Ending Page	673
Page Count	4
File Format	PDF HTM / HTML
DOI	10.3762/bjoc.16.64
PubMed reference number	32362944
Journal	Medline
Volume Number	16
Alternate Webpage(s)	https://www.beilstein-journals.org/bjoc/content/supplementary/1860-5397-16-64-S1.pdf
Alternate Webpage(s)	https://www.beilstein-journals.org/bjoc/content/pdf/1860-5397-16-64.pdf
Alternate Webpage(s)	https://doi.org/10.3762/bjoc.16.64
Journal	Beilstein journal of organic chemistry
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article

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